@aparrish
This makes me think of the idea of 'hacking' as part of a trickster mentality, as well, since violations of gender roles are strongly associated with general violations of social roles.
To suddenly veer into a different domain entirely: media theorists focusing on anime have alternate genres, & a big one is the 'carnivalesque', in which social roles or their representations are inverted for comedic or horrific effect. Carnival & saturnalia definitely featured cross-dressing.